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Liquid Chromatographic Properties and Aqueous Solution Stability of N-hydroxy-3,4-methylenedioxyamphetamine

Liquid Chromatographic Properties and Aqueous Solution Stability of N-hydroxy-3,4-methylenedioxyamphetamine

A K Valaer, W R Ravis, C R Clark

J Chromatogr Sci. 1990 Sep;28(9):482-6.

PMID: 2273071

Abstract:

The reversed-phase liquid chromatographic properties of N-hydroxy-3,4-methylenedioxyamphetamine (NOHMDA) were determined on a C8 stationary phase specifically prepared for the separation of basic compounds. NOHMDA and several N-alkyl MDA derivatives displayed excellent peak shape on this stationary phase without the need for competing bases such as triethylamine. The k' values for NOHMDA varied with mobile phase pH in the range of 2.5 to 6.0, but the retention of the primary amine, MDA, and N-alkyl MDAs remained relatively constant over this range. The pKa value for NOHMDA was determined by titration to be 6.22 compared to a pKa of 10.04 for MDA. Thus, the variation of k' with mobile phase pH for NOHMDA may be a result of appreciable changes in degree of protonation. The stability of NOHMDA was found to decrease with an increase in aqueous solution pH. At pH 7.0 the degradation half-life was determined to be 49.8 h, which decreased to 2.57 h at pH 10.0. Above pH 10.0 the decomposition to the corresponding oxime was too fast for a reliable half-life determination.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP114562593	(±)-N-Hydroxy-3,4-methylenedioxyamphetamine		114562-59-3	Price

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